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3,4,5-trisubstituted-4,5-dihydroisoxazole, derivative and synthetic method and application thereof

A technology of dihydroisoxazole and three substitutions, applied in 3 and 4, can solve the problems of cumbersome steps and achieve the expected effect of simple reaction system, high product utilization value and market commercialization prospect

Inactive Publication Date: 2017-08-04
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are few reports on the synthesis methods of isoxazole compounds at home and abroad, and the published literature is limited to only a few and the steps are cumbersome.

Method used

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  • 3,4,5-trisubstituted-4,5-dihydroisoxazole, derivative and synthetic method and application thereof
  • 3,4,5-trisubstituted-4,5-dihydroisoxazole, derivative and synthetic method and application thereof
  • 3,4,5-trisubstituted-4,5-dihydroisoxazole, derivative and synthetic method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0135] The NMR and mass spectrometry data of embodiment 1 product are as follows:

[0136] 1H NMR (400MHz, CDCl3) δ7.69 (dd, J = 6.6, 2.9Hz, 2H), 7.58 (d, J = 7.3Hz, 1H), 7.42–7.39 (m, 3H), 7.31–7.24 (m, 3H), 6.05(dd, J=11.1, 6.9Hz, 1H), 3.96(dd, J=16.8, 11.2Hz, 1H), 3.23(dd, J=16.8, 6.9Hz, 1H).13C NMR(101MHz, CDCl3)δ156.13,138.97,131.11,130.22,129.47,129.19,129.03,128.69,127.18,126.75,126.61,79.44,77.32,77.00,76.68,42.72. 258.06802,found258.06799.

Embodiment 2

[0137] The NMR and mass spectrometry data of embodiment 2 product are as follows:

[0138] 1H NMR (400MHz, CDCl3) δ7.87 (td, J = 7.6, 1.6Hz, 1H), 7.56 (dd, J = 7.6, 1.6Hz, 1H), 7.41–7.35 (m, 2H), 7.31–7.22 ( m,2H),7.18(td,J=8.0,1.2Hz,1H),7.12–7.07(m,1H),6.03(dd,J=11.2,7.2Hz,1H),4.06–3.98(m,1H) ,3.34–3.27(m,1H).13C NMR(101MHz,CDCl3)δ160.27(d,J=252.9Hz),152.97(d,J=3.1Hz),138.78,131.84(d,J=8.6Hz) ,131.15,129.48,129.03,127.13,126.52,124.42(d,J=3.4Hz),117.28(d,J=11.6Hz),116.50,116.28,79.62(d,J=2.3Hz),77.32,77.00,76.68 ,44.26(d,J=6.8Hz).HRMS(ESI)m / z calcd for C15H12ClFNO+(M+H)+276.05860,found 276.05908.

Embodiment 3

[0139] The NMR and mass spectrum data of embodiment 3 product are as follows:

[0140] 1H NMR (400MHz, CDCl3) δ7.65–7.59(m,2H),7.41–7.23(m,6H),6.06(dd,J=11.0,7.1Hz,1H),4.08(dd,J=17.3,11.0 Hz,1H),3.36(dd,J=17.2,7.1Hz,1H).13C NMR(101MHz,CDCl3)δ156.11,138.53,132.79,131.15,130.89,130.52,130.47,129.48,129.07,128.62,127.190,126. 126.61,80.01,77.32,77.00,76.68,44.92.HRMS(ESI)m / zcalcd for C15H12Cl2NO+(M+H)+292.02905,found 292.02936.

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Abstract

The invention relates to 3,4,5-trisubstituted-4,5-dihydroisoxazole, a derivative and a synthetic method and an application thereof. The invention mainly relates to a synthetic method of an isoxazoline compound. With adoption of a technical scheme that an aldehyde compound and oxime ester are converted into isoxazoline and the derivative thereof by taking an organic solvent as a solvent under the action of alkali without using a catalyst, the synthetic method solves the problem that an existing synthetic method of the isoxazoline compound is complicated in synthetic step, is accomplished by adopting multiple steps, and also needs a metal catalyst, a chemically equivalent metal oxidant or a peroxide. The atom economy is kept to the extreme extent; the isoxazoline compound has a stable molecular structure and an excellent chemical property, and molecular slices and compound segments contain rich contents with biological activity and pharmacological activity. The isoxazoline compound also has the characteristics of being simple in reaction system, mild in reaction condition, relatively less in reaction equipment, simple in experimental operation, wide in source of materials, high in yield, easy for expansion of user and application, relatively high in utilization value of product and expectable in market commercial prospect.

Description

technical field [0001] The present invention relates to an organic compound and its synthesis method, in particular to a 3,4,5-, trisubstituted-4,5-dihydroisoxazole, derivatives, its synthesis method and application. Background technique [0002] Isoxazole and its derivatives are a very important class of organic heterocyclic compounds, widely used in organic synthesis. This kind of compound has good biological activity and pharmacological activity, so it has extremely high application value in the fields of pesticide and medicine. Isoxazole compounds are now mainly used in the research of herbicide, bactericide, insecticide and pharmacological activity, many of which have been developed into herbicides (such as clomazone), fungicides (hymexazol), insecticides ( Oxazophos) and other pesticide chemicals and pharmaceutical intermediates. Some sulfa drugs also contain isoxazole rings, such as sulfamethoxazole. So far, there are few reports on the synthesis methods of isoxazo...

Claims

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Application Information

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IPC IPC(8): C07D261/04C07D413/04C07D261/20C07D498/04A01N43/90A01N43/80A01P13/00A01P1/00A01P3/00A01P7/04
CPCA01N43/80A01N43/90C07D261/04C07D261/20C07D413/04C07D498/04
Inventor 黄华文李飞飞邓国军肖福红
Owner XIANGTAN UNIV
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